To casual movie-goers, the idea of comparing Iron Man to Batman seems logical, considering the superficial similarities between the two. But if you'll try to compare the two based on the question which one is darker as a character, a lot of people will find that confusing, considering that Iron Man they know is not dark in the slightest. But if you're familiar with the comic book Iron Man in some shape or form, that comparison is fair, considering how distinctly grimmer the comic book Iron Man is in comparison to his lighter version from movies. So let's compare who's a more brooding bad-ass - Iron Man or Batman.
WHOSE ORIGIN IS MORE COMPLEX?
If Bruce Wayne's origin was about him genuinely trying to find purpose in his life to spare himself of guilt he felt over his parents' death, Tony Stark became Iron Man over necessity. It wasn't a non-ego-based decision but rather the extreme circumstances in which he was surrounded that required him to create that suit and save his life.
So here you have genuine desire to help people vs. someone's ego. And let's not forget the fact that Tony Stark was not a very noble man before he decided to become Iron Man; being a war profiteer who showed very little concern about his input in global wars, while Bruce Wayne was, if not a perfect man, at least not as controversial as a person.
But, to me, doing a selfless act of duty, risking your life, and lives of the people close to you, because you believe in what is right, despite all the odds, seems more complex than being thrown in a situation with no choice.
THE WINNER: BATMAN
WHO HAS BIGGER PARENTAL ISSUES?
Well, Batman sure has issues, and so does Iron Man. However, if you don't count the death of Bruce's parents as part of the issue, his relationships with his parents were healthy, to say the least.
Iron Man, on the other hand, wasn't as lucky, since he had very troubled childhood and was in conflict with his parents since he was a child.His father was from time to time abusive towards him, and was, in fact, the main factor that caused in Tony his drinking habits.
So If Bruce felt alone his entire life because his parents, that he loved, were taken from him, Tony felt alone because his parents forced him to want to be alone.
THE WINNER: IRON MAN
WHO HAD BIGGER TROUBLES WITH WOMEN?
Now this is a tie between the two, because both had a very rough time when it comes to having relationship with women. With Batman you have constant clashing between him and Catwoman. But then you also have characters like Talia, who did all sorts of nasty things towards him.
With Iron Man you a very similar situation with the character of Madam Masque, who's also an arch-villain/love interest like Talia.
But, the worst case of these two characters being victims of unhealthy relationships must be when Talia killed her and Bruce's son, Damian, and when Kathy Dare, an obsessive stalker of Tony Stark, shot him out of a blue, thus paralyzing him.
And while Damien came back, and Tony could walk again, seeing your child getting killed in front of your eyes is worse than being in a wheelchair, despite the fact that both of these consequences did not last for too long.
THE WINER: BATMAN
WHO’S A BIGGER MESS AS A PERSON?
Now that's an intricate question. With Batman there's for sure a lot of insecurities and flaws. However, one of the thing that always defined him is his self-dedication and unwillingness to ever give up. Sure, there were some stories where he acted the opposite. But, in general, Batman is always confident in what his mission in life is, and he never wants to give up.
With Iron Man it's a much different story, because he, very much, have given up more times than superhero can allow himself. Iron Man is very flawed as a person. But flawed not in the sense that he has bad habits; he flawed in the sense that he has, what seems like, an inferiority complex.
Iron Man is a very self-critical person. A man who sometimes has such animosity towards himself, he could punch his own reflection in the mirror. The most obvious example of that happened when Obadiah Stane took over Tony's company, thus left Tony homeless, where he was crawling around filthy streets, drinking, and admitting to himself that his life has no meaning and he'd rather be dead.
And that's something I never saw Batman being. I never saw Batman being broken to such extents. Which is why, I think, Iron Man is a much darker character than Batman in this regard.
AND THE ULTIMATE WINNER IS…
THE POWER OF FRIENDSHIP! (AND MONEY.)